


Worth the Wait

by Lopsided_Whiskey_Grin



Category: Supernatural
Genre: Alcohol, Blow Jobs, Bottom Dean, Dean Winchester's First Time, First Time, Loss of Virginity, M/M, Sam is 17, Top Sam Winchester, Virgin Dean Winchester
Language: English
Status: Completed
Published: 2017-11-14
Updated: 2017-11-14
Packaged: 2019-02-02 05:32:18
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,830
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12720618
Author URL: https://archiveofourown.org/users/Lopsided_Whiskey_Grin/pseuds/Lopsided_Whiskey_Grin
Summary: Dean Winchester is twenty-one and he has a secret. For all his macho posturing and supposed sexual bravado, he is still a virgin. He's kept this secret so well even his own brother doesn't know the truth. And it is because of his brother, in fact, that he's kept up this facade for so long; coming up with stories of his many conquests and staying out until all hours of the night, to give the impression that he's a casanova heartbreaker so no one, especially not Sam, will know the truth is a wall he's painstakingly built around himself for years.  But the truth of the matter is, he has never actually gone all the way and it's because the only one he wants is Sam.





	Worth the Wait

Dean Winchester is twenty-one and he has a secret. For all his macho posturing and supposed sexual bravado, he is still a virgin. He's kept this secret so well even his own brother doesn't know the truth. And it is  _ because _ of his brother, in fact, that he's kept up this facade for so long; coming up with stories of his many conquests and staying out until all hours of the night, to give the impression that he's a casanova heartbreaker so no one,  _ especially not Sam,  _ will know the truth is a wall he's painstakingly built around himself for years. 

The fact is Dean wants Sam in a way he knows a brother shouldn't. He knows it's wrong and immoral and all those other shameful words people would use to describe the thoughts he has of his little brother. He's tried going home with girls, he's tried hooking up with guys in deserted locker rooms, but it has never felt right. He has never actually gone through with it all the way and it's because the only one he wants is Sam. 

To put it simply, Dean is in love with him. The kind of love that transcends thought or reason. The kind of love that is all consuming and impossible to ignore. The kind of love that feels like burning and drowning all at once. But he can do nothing about it so he does nothing about it. 

One night though, everything changes. Dad is gone again, and it's just Sam and Dean in the motel room. Dean is actually old enough to buy liquor legally and he does -- with a stolen credit card of course -- he has a reputation to keep up after all. He buys a big bottle of cheap whiskey and a sixer of import with the intent of getting full on blasted. It'll help him fall asleep cause on nights like these, when he wants Sam more than ever, his brain will work overtime at the expense of some much needed REM.

Dean's sitting up against the headboard, pulling off a slug of Kentucky Deluxe right from the bottle and watching the highlights of last night's game on ESPN. He's already feeling pretty toasty from the booze and is considering just falling asleep right there.

But then Sam comes in the door from a night of pickup basketball with kids from the neighborhood and Dean simultaneously perks up and groans inwardly. Sam is ruddy-cheeked and gleaming with sweat that darkens patches at his shirt’s armpits and down the back. His hair is floppy with the moisture. 

Dean watches him cross the room to the bathroom with a tension tightening his belly. Sam pulls his damp shirt over his head and Dean has to look away. He takes another deep pull of his whiskey and tries to put all his focus on the tv. 

But then Sam crosses back toward him wearing only his shiny basketball shorts slung low on his skinny hips. A hint of dark, fine hairs leaves a trail from his navel down under his waistband and Dean's mouth goes dry. He takes another sip of liquor. 

Sam gives a passing glance to the television then deliberately climbs up onto the bed. He sits on his knees down by Dean's crossed ankles and tilts his head to the side with a smirk. 

“Can I have some?” he asks. 

Dean passes him the bottle and watches closely as Sam swallows it down. After Sam has taken a long drink he hands it back and gives Dean a long, appraising look. 

Dean squirms under Sam's scrutiny. “What?” he huffs finally, subconsciously rubbing the pad of his thumb over the lip of the bottle where Sam's mouth had just touched. 

He brings the Deluxe up, about to take another drink. His heart is pounding heavy in his chest at how close Sammy is. 

“You tell me,” Sam says. He starts crawling toward Dean and Dean instinctively backs up, but the headboard behind him stops him from going anywhere. “I've seen the way you look at me, Dean. And if you're not gonna make the first move, I will.”

Dean swallows hard against a suddenly dry throat. “What are you talking about?” he asks, his voice creaky, uneven.

Sam straddles Dean's lap and cocks his head to the side, causing his bangs to flop into his eyes. Dean cannot explain why this is one of the sexist things he's seen. 

“I've been around enough to know what it means when someone looks at you the way you look at me,” Sam says softly, bringing his hands to Dean's sides. 

Dean can't seem to really comprehend Sammy’s words. He's been around? How many times has he been around? When did he find the time to make this happen without Dean knowing? Dean feels a pinch of jealousy but he swallows it down; he supposes they both have their share of secrets. 

Sam's hands move up Dean's stomach until they are resting on his rapidly rising and falling chest. “And what does it mean?” Dean counters breathlessly. 

Sam smiles and curls in close to Dean's face. Dean can smell the hint of whiskey on Sam’s mouth and a strong whiff of male sweat drifting up from Sam’s body and his cock starts filling rapidly. 

“It means you want me, Dean.” Hazel-blue eyes gaze at him from under long lashes.  Dean stays silent -- words refuse to form on his lips. “Isn't that the look you've given all those other people you've been with?” Sam asks, hesitantly. For the first time he looks a little uncertain.

Dean pulls in a shuddering breath through flared nostrils. He can't fight his feelings any longer -- and he can't lie to Sammy anymore.

Dragging his eyes up along Sammy’s naked torso, he says “I've never been with anyone.” He can't quite pull his gaze up beyond Sam's collarbones. 

He can hear Sam suck in a breath and Dean's cheeks pink immediately. The tips of his ears are burning. And he still doesn't look up. 

Sam's long, thin fingers move down to Dean's sides and flex a little and he shifts on Dean's lap. “No one? Not ever?” Sam asks after what feels like an eternity. 

Dean shakes his head and finally looks up. Sam's eyes are wide, but not in a mocking way -- more like a “ _ my world was completely just rocked”  _ kind of way.

“Why not?” Sam whispers, almost like he knows the answer already. 

Dean considers the question, his jaw working and fear coiling in his belly. “Because I only want you, Sammy.” He huffs out a humorless laugh and gives his head a little shake in disbelief that he's actually said the words out loud. 

Dean can see Sam's throat bob as he swallows and the next thing he knows, Sammy is cupping his face with warm hands and crashing his mouth against his own. Dean is so shocked by it that he freezes, doesn't even breathe. His hands are stuck down by his sides, one holding the whiskey bottle in a white-knuckle death grip, the other fisted in the motel sheets. 

But then Sammy grinds down in his lap and Dean’s lips fall open in a moan. Sam takes full advantage and plunges his tongue deep inside, his hands still framing Dean’s jaw.

While Dean may be a virgin, he’s at least been kissed before. Though truthfully, he’s never been kissed like this. His mouth begins moving of its own accord, taking taste after taste of his little brother. It's something he's wanted for forever and his body captures what it has desired for so long before his brain has a chance to fully process the situation.    

Soon though, the realization of what he's doing hits him hard, like a cold slap to the face. Tearing his mouth away from Sammy’s nearly kills him, but he does it.

He's gasping for breath with his hands still planted firmly at his sides. Sam is sitting in his lap, nestled perfectly on top of Dean's throbbing cock. It feels so indescribably perfect, Dean can't quite bring himself to push Sammy off of him. 

Sammy makes a noise of protest and tries going in for another kiss, but Dean holds him back. 

“We can't do this, Sammy,” Dean says, damn near driven out of his mind by the lingering taste of Sam on his tongue. “It's wrong.”

Sam almost looks wounded. He sits back a little and his hands settle on Dean's hips. His eyes dip down to the buttons on Dean's flannel overshirt. 

“Does it  _ feel _ wrong?” The words are almost a whisper. He fingers Dean's belt loops and looks up slowly, pinning Dean's gaze like a butterfly to a board. He rocks his ass on Dean's crotch with the barest hint of movement and Dean has to work very hard to bite back the moan rising up in his throat. 

Dean can't seem to form a reply. He stares at Sam helplessly. He's spent so long meticulously building the walls around his heart that he struggles to even admit to himself that what Sam is doing to him actually feels the very opposite of wrong.

Sam’s face is a close study in somber thoughtfulness as he curls toward Dean again. He squeezes Dean's hips gently and drags his nose up the side of Dean's neck, huffing softly against the sensitive skin there. A full body shudder wracks Dean down to his goddamn soul.

Sam nuzzles into the spot where Dean's neck meets his shoulder. “Does this feel wrong?” he whispers, moving his head up to draw Dean's earlobe between his teeth. 

Dean sucks in a sharp breath and shakes his head. It feels incredible and beautiful and freeing and anything but wrong. 

Sam hums his approval and presses his mouth to Dean's thundering pulse point. Then he grabs blindly for Dean's hand and brings it right to his crotch so Dean can feel his erection straining against his silky shorts. 

“Does this feel wrong?” Sam breathes the words in a hot rush across Dean's jaw. 

Molten arousal pools heavy in Dean's groin and his hips jerk up. His own cock is hard enough to cut diamonds where it's confined and throbbing down the left side of his pant leg. 

“G-god,” Dean stutters, squeezing his eyes shut. “Sammy.” It's all he can say. It's a prayer and a plea all at once. He's crumbling and drowning and soaring and he never wants these feelings to stop.

“It doesn't feel wrong ‘cause it's not wrong, Dean,” Sam murmurs, pushing his chest to Dean's so he can wrap his arms around him and dip his fingers down the back of his jeans. 

Dean's hips jerk again when one of Sam's dry, slender fingers wedges into his crack. “Please,” Dean whispers against Sam's cheek. 

He can feel Sam nod just a little and then he’s pulling back and tugging his fingers from Dean’s waistband. Sam sits back again in Dean’s lap, applying a delicious amount of pressure to his aching yet still unsatisfied member. Without another word, Sam slips Dean’s over shirt from his shoulders. Dean has to lean forward away from the headboard to help him get it off. Next, Sam grabs the hem of Dean’s tee and tugs it up over his head with Dean’s help again. 

And then Sam’s mouth is on his once more. This time, Dean lets his hands roam free. They card through Sammy’s hair and run up and down his bare back. They squeeze at his narrow hips. They frame his perfect cheeks. His hands cannot touch in enough places -- they're everywhere. 

The kiss continues on and is deep and frenzied and by the time they pull apart again, Dean is panting for breath just like Sam is. Dean looks into Sam's eyes. His pupils are huge, leaving only a thin ring of his irises visible. 

“Can I?” Sam asks reverently. His breath is sweet and hot where is washes over Dean's chin. 

Dean swallows. “What?” His voice shakes just a little. 

“Can I be your first?”

It's like Dean has been waiting his whole life for this question, and he has. He doesn't hesitate to reply. “Yes.”

Sam makes the most amazing noise of approval low in his throat and Dean almost comes undone then and there. Sam gets off the bed slowly then pulls down his basketball shorts. He's not wearing anything underneath. 

The sight of Sammy standing there -- completely nude, his teenage body thin but strong, his cock curving so beautifully, his face sincere yet eager -- makes Dean feel like he is finally,  _ finally _ , right where he belongs.

Sam holds his hand out toward Dean and beckons him off the bed. Dean complies, slides to the side of the motel room mattress, then stands before Sammy bare chested with his jeans slung low on his hips. Sam has gone through a growth spurt in the last six months or so and now stands almost eye to eye with Dean. 

Dean takes a deep breath then puts his hands on his pants, about to undo the button. But Sam reaches out and stops him. 

“Let me,” he says. 

Nodding wordlessly, Dean lets his hands fall to his sides. Sam steps closer, his cock bobbing with the movement. He undoes Dean's pants with a sure flick of his wrist and pulls down his fly. 

Dean's pulse is thundering away in his throat as Sammy hooks his thumbs in his jeans and tugs his pants and boxers down at the same time. They pool at his feet and he steps out of them gingerly. 

Sam looks up at him through his lashes and heated tendrils of pure desire curl through Dean's entire body. Sam kneels down in front of Dean and gently grasps his hardened cock at the base. Licking his lips to wet them, Sam begins pushing his mouth down Dean's dick before Dean fully has a chance to prepare himself. 

Dean's knees buckle and his eyes flutter closed. The hot, wet feel of Sam all around him has him seeing stars. His hands blindly find Sam's long hair as Sam begins bobbing up and down on his cock and he runs his fingers through the locks, stiff with sweat from his basketball game. Sam moans around his member when Dean tugs at his roots and Dean jerks his hips forward involuntarily. 

“S- sorry!” Dean blurts out when Sam gags. He pulls his dick from Sam's mouth immediately, his face burning with embarrassment. 

Sam looks up at him and shakes his head with a smile. His cheeks are flushed. He runs the back of his hand across his lips as he says, “It's okay, Dean. I like getting choked by you.”

A flush of excited pride rushes through Dean and he cups Sam's cheek with his hand. Sam nuzzles into Dean's touch then looks up at him, his face sexy and coy. 

“Get up on the bed for me, okay?” Sam asks, but it sounds more like a demand than a request. 

Dean shivers and nods his head. He climbs onto the bed as he's told. He's about to flop down on his back but Sam's warm hand touching his hip holds him as he is on hands and knees. 

“Stay just like that,” Sam says. 

Dean feels the bed dip down when Sam climbs up behind him. He has just a moment to ponder the possibilities of this angle and he hopes with everything inside him that he'll finally feel Sam's tongue opening him up like all those nights he spent fantasizing about it. 

After two agonizing seconds, Dean's dreams finally come true. Sam takes two big handfuls of his ass cheeks and pulls them apart. Dean sucks in a sharp breath as his virgin skin is suddenly exposed to the air. He lets the air out of his lungs with a whoosh when Sam's tongue prods gently at his hole. 

He tenses up without thinking about it and Sam gives a chuckle behind him; Dean can feel the staccato rush of his breath across his skin. 

Sam squeezes his cheeks soothingly. “Relax, Dee, it's just me.”

Dean nods and sinks his face down onto his forearms. Sam groans at the higher angle of Dean's ass and he dives right back in. Dean suddenly becomes a sloppy, shuddering mess under the relentless ministrations of Sammy’s mouth. His thighs are shaking and he's moaning uncontrollably by the time Sam is able to spear his tongue almost all the way inside Dean's hole. 

Sam pulls back and Dean whimpers at the sudden emptiness. “God, Dean, you should see what I'm seeing right now. So beautiful.” He dips the tips of his thumbs into Dean's slack hole and pulls apart a little. Dean's aching cock drips a thick line of precome down onto the sheets. “I think you're ready.”

Dean nods his agreement adamantly, shoving his face into the mattress. “Please, Sammy,” he begs. He wants nothing more than to be filled by his little brother for the very first time. He wants nothing more than this. 

He hears Sam pull in a deep, serious breath. And then there's a dip in the bed as Sam repositions himself and the sound of a plastic cap being cracked open. The blunt head of Sam's dick, slippery and hot, is suddenly pressing against Dean's quivering entrance. 

Dean makes a conscious effort to relax his body. But he's too wound up from wanting this for so damn long. Sam rubs circles into Dean's right hip with his palm and grunts as he starts pushing forward. 

The burn is simultaneously phenomenal and terrifying. Dean knows Sam has a surprising  girth for his thin frame and he has no idea how his body will accommodate such a size. He tenses up, going rigid, worrying about how much this is going to hurt. 

Sam immediately stops moving forward and drapes his long body over Dean's back so he can whisper in his ear. “Take a deep breath, Dean. It’s okay. Let me in,” he coaxes. He mouths a tender kiss to the side of Dean's neck, laying all his fears to the wayside.

Dean pulls in a deep, deep breath and lets it out slowly through pursed lips. After a moment, he feels his body go slack, feels his hole become lax. Sam must be able to feel it too because he sits back up again and starts pushing in. This time there's far less resistance. There is a small pinch of pain when the rigid crown of Sam's cock finally breeches him, but the pleasure overshadows it almost completely. 

“Oh god, Sammy,” Dean murmurs. 

“Just you wait, Dee. It gets even better.”

And oh god, does it ever. Sam clamps his hands on Dean's hips and starts sliding forward until the entire length of him is enclosed deep inside Dean’s body. They are body to body, skin to skin, and Dean could not have ever imagined it ever feeling this fucking good. He is stuffed full of Sam's hot, throbbing member and he could positively die from the perfection of it. 

But then… then Sam starts to move. He pulls almost all the way out and pushes forward all the way again in one smooth stroke. Dean gasps and fists his hands into the sheets. His dick continues to weep with precome but he doesn't want to touch himself yet. He wants to focus all his attention on this moment, of Sam moving in and out of him, of being filled and fucked, _ finally _ . 

His breath starts coming in harsh pants as Sam builds a tortuous tempo, snapping his hips forward and back, slamming against Dean hard enough to push him up the mattress, hard enough to thump the headboard against the wall. 

Dean's legs threaten to give out with the brutal onslaught and his thighs spread a little wider, bringing him closer to the bed. Sam thrusts down into him and Dean can't help but cry out. All his nerve ending light up with the way Sam's cock is nailing his prostate with each downstroke. Dean literally has no words to describe the ecstasy. A litany of incoherent praises and curses tumble from Dean’s lips where his face is screwed down into the mattress beneath him.  

“Oh, fuck. Dean, oh fuck,” Sam groans behind him and his movements become erratic, frantic. He reaches his hand beneath Dean and grasps his drooling cock. Dean bucks against him at the unexpected touch and inadvertently draws Sam deeper inside him than ever before. Both moan. Dean sees a billion stars explode behind his tightly closed eyes.

Sam starts pumping his hand in an alternating tempo to the thrusts of his hips and Dean spasms wildly, desperately trying his fuck into Sam's grip. He is sweating and swearing and shaking and utterly falling apart under Sam. He wants to come, he needs to come, he'll die if he doesn't  _ fucking come _ . But he also doesn't want this to ever end. He wants to stay fused to Sam forever, wants to be filled and warmed from the inside out by his baby brother.

But at the moment he has no control over his own body and he has no choice. Two more pumps of Sam's hand and three more deep penetrations from Sam's dick and Dean is positively done for. His whole body quakes as he reaches completion. 

He sobs out Sammy’s name as his release spills out of him in gleaming, pearly ropes that stripe the sheets. Sam shudders behind him as Dean's body tightens up and he lays heavy on Dean’s back as he comes deep inside. Dean can feel the warmth of Sam’s spend filling him up and his cock gives another weak spurt in response. 

Utterly drained, Dean collapses right onto the wet spot with Sam still draped over his back and lodged deep in his ass. He turns his head to the side, trying to catch his breath. His mouth is met by Sam’s. Dean grins as Sam kisses him, he can’t help it. Even in his wildest dreams he never imagined it could be like this. 

Sam chuckles softly and presses another kiss to the corner of Dean’s sated smile. “Was it worth the wait?” he asks hoarsely.

“Oh hell yeah.” Dean kisses Sam back and wriggles his hips a little, earning a gasp from his brother. He can feel Sam’s cock give a twitch and his own throbs in response. “I’d wait a hundred years if it meant you’d be my first.” 

Sam runs his fingers through Dean’s hair and mouths a kiss to the freckles on his left shoulder. He slowly starts rutting against Dean’s ass. Dean moans as Sam’s dick starts thickening up again. 

“Can I be your second, too?” Sam asks, his voice husky. 

Dean doesn’t have to respond. He knows Sam already knows the answer to that.     
  



End file.
